O'Hare Intl

$149+ Cheap flights from Toronto (YTO) to O'Hare Intl (ORD)

YTO — ORD
Dec 11 — Dec 181
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Toronto to Chicago O'Hare Intl are usually found in September or April, booked 84 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap flight deals from Toronto to O'Hare Intl

Cheapest flights from Toronto to O'Hare Intl

Fri 12/114:35 pm -
Nonstop2h 05m
Mon 12/146:20 pm -
Nonstop1h 45m
Deal found 11/9$234
Mon 12/710:29 am -
Nonstop2h 05m
Mon 12/76:20 pm -
Nonstop1h 45m
Deal found 11/10$240
Tue 12/14:35 pm -
Nonstop2h 05m
Tue 12/812:15 pm -
Nonstop1h 45m
Deal found 11/9$241
Mon 12/2110:29 am -
Nonstop2h 05m
Sun 12/276:20 pm -
Nonstop1h 45m
Deal found 11/10$243
Tue 12/14:35 pm -
Nonstop2h 05m
Fri 12/412:15 pm -
Nonstop1h 45m
Deal found 11/9$249
Mon 12/2110:29 am -
Nonstop2h 05m
Tue 12/2912:15 pm -
Nonstop1h 45m
Deal found 11/10$253
Fri 12/254:35 pm -
Nonstop2h 05m
Tue 12/2912:15 pm -
Nonstop1h 45m
Deal found 11/10$254
Sat 12/54:35 pm -
Nonstop2h 05m
Sat 12/126:20 pm -
Nonstop1h 45m
Deal found 11/10$255
Mon 11/234:35 pm -
Nonstop2h 05m
Mon 11/306:20 pm -
Nonstop1h 45m
Deal found 11/9$256
Mon 11/238:20 am -
Nonstop2h 03m
Sun 11/298:45 am -
Nonstop1h 42m
Deal found 11/9$257
Mon 11/2310:45 am -
1 stop5h 15m
Sat 11/281:55 pm -
Nonstop1h 47m
Deal found 11/9$257
Thu 11/269:50 am -
1 stop6h 12m
Sun 11/297:05 am -
1 stop6h 16m
Deal found 11/9$258

Find flight deals from Toronto to O'Hare Intl

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$234
(Super.com)

One-way from

$149
(Kiwi.com)

Popular in

January

Cheapest in

September

Average price

$345

Good round-trip deal

$268 or less

Good one-way deal

$219 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago O'Hare Intl flight deals.
Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago O'Hare Intl flights.
From Toronto (YTO) to Chicago O'Hare Intl
One-way flight from Toronto (YTO) to Chicago O'Hare Intl
Highest demand for flights based on searches. 5% potential increase in price ($18 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Average for round-trip flights in November 2026
Price to beat on a round-trip flight from Toronto (YTO) to Chicago O'Hare Intl.
Price to beat on a one-way flight from Toronto (YTO) to Chicago O'Hare Intl.

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Toronto to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 12/1

4:35 pm-5:40 pm

Nonstop2h 05m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$158

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 12/29

4:35 pm-5:40 pm

Nonstop2h 05m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$168

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Mon 12/14

4:35 pm-5:40 pm

Nonstop2h 05m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$169

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Sat 1/16

8:20 am-2:52 pm

2 stops7h 32m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$175
Quickest round-trip

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Thu 3/25

10:35 am-11:30 am

Nonstop1h 55m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$177

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 12/10

6:45 am-7:54 am

Nonstop2h 09m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$180

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 12/7

5:55 pm-7:05 pm

Nonstop2h 10m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$180

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 1/14

3:35 pm-4:50 pm

Nonstop2h 15m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$180

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 1/1

7:26 pm-8:40 pm

Nonstop2h 14m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$180

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 11/25

6:40 pm-12:01 am

1 stop6h 21m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 47 resultsSorted by cheapest first
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Compare providers for flights from Toronto to O'Hare Intl

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Toronto to O'Hare Intl in November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Toronto-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toronto-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toronto-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toronto-Chicago O'Hare Intl Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Toronto-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Toronto to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Toronto with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Toronto to Chicago O'Hare Intl Airport

What is the cheapest month to book a flight from Toronto to Chicago O'Hare Intl Airport?

Currently, February is the cheapest month in which you can book a flight from Toronto to Chicago O'Hare Intl Airport (average of $284). Flying from Toronto to Chicago O'Hare Intl Airport in November is currently the most expensive (average of $368). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YTO to ORD?

When flying from Toronto to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 31% versus a flight in the afternoon.

Weekly flight availability from Toronto to Chicago O'Hare Intl Airport

The most flights from YTO to ORD are scheduled on a Monday (68 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (44 on average).

How much does it cost to fly round-trip from Toronto to Chicago O'Hare Intl Airport?

Airfare is below average for this route at the moment.
Toronto to Chicago O'Hare Intl Airport flights typically cost between $248 and $433 in December.
The cheapest round-trip price found within the last 5 days was $234 on Porter Airlines (Dec 11-Dec 14).

How often are flights from Toronto to Chicago delayed?

About 13% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 139 minutes.

What is the most punctual flight time for Toronto to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Toronto to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 9% of flights being delayed.

How far ahead should I book a flight from Toronto to Chicago O'Hare Intl Airport?

The best time to book flights from Toronto to Chicago O'Hare Intl Airport is 87 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest day to fly from Toronto to Chicago O'Hare Intl Airport?

Travelers seeking maximum savings on their Toronto to Chicago O'Hare Intl Airport flight should consider departing on Sunday at noon when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Toronto to Chicago O'Hare Intl Airport flights

Cheapflights partnered with top experts to bring you the best recommendations for your Toronto to Chicago O'Hare Intl Airport trip
Our travel experts
Gabriel Leigh

Gabriel Leigh

Expert on British Airways

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Jessica Macdonald

Jessica Macdonald

Expert on Air Canada

Currently based in Scotland after living in South Africa and the United States, Jessica has been writing travel and aviation content for more than 10 years. She regularly contributes to Travel + Leisure and TripSavvy, and has had work published by Condé Nast Traveller and The Independent. She has traveled to more than 50 countries across six continents.

Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Ramsey Qubein

Ramsey Qubein

Expert on ORD

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Kaitlyn McInnis

Kaitlyn McInnis

Expert on YYZ

Kaitlyn is a guidebook author and travel writer splitting her time between Atlantic Canada and Istanbul, Türkiye. She has visited over fifty countries and all seven continents, so she is very familiar with many hotels, airports and airlines around the globe. But her favorite type of vacation is sunbathing by the sea with a good book in hand.

Reviews of airlines servicing O'Hare Intl

Read reviews from past customers who have flown Porter Airlines,United Airlines, andAir Canada from Toronto to Chicago O'Hare Intl Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

6.9

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Entertainment

6.9

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Entertainment

6.9

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Entertainment

6.9

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Entertainment

6.9

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Related info for your journey

  • How long is the flight from Toronto to Chicago O'Hare Intl Airport?

    Airlines like Porter Airlines, United Airlines, and Air Transat fly from Toronto to Chicago O'Hare Intl Airport in about 1h 55m. The time it takes to get you to your destination can typically vary by up to 3h 48m. The distance from Toronto to Chicago O'Hare Intl Airport is about 445 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Toronto to Chicago O'Hare Intl Airport round-trip?

    Currently priced at $137, Air Canada will fly you from Toronto to Chicago O'Hare Intl Airport and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and United Airlines - these airlines can fly you to your destination from $193 and $195, respectively. Air Canada is priced at 57% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Toronto to Chicago O'Hare Intl Airport one-way?

    For one-way options, check prices for Air Canada. According to our data, you can fly for as low as $126. Users have also found prices from $126 and $130 on United Airlines and American Airlines, respectively.

  • What are the most popular routes from Toronto to Chicago O'Hare Intl Airport?

  • What are the most reliable airlines from Toronto to Chicago O'Hare Intl Airport?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Toronto to Chicago O'Hare Intl Airport on time: Sun Country Air (100%), Royal Jordanian (91%), Copa Airlines (88%).

  • What are the cheapest flights from Toronto to Chicago O'Hare Intl Airport?

    While on average a flight from Toronto to Chicago O'Hare Intl Airport is generally $1,194, our data shows the cheapest flight currently is $171. When looking at the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), you can expect to pay $272 for that flight.

  • Can I find deals for flights from Toronto to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Toronto to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Toronto to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Toronto to O'Hare Intl.

  • Can I find deals for business class flights from Toronto to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Toronto to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Toronto to Chicago O'Hare Intl Airport?

    Currently, February is the cheapest month in which you can book a flight from Toronto to Chicago O'Hare Intl Airport (average of $284). Flying from Toronto to Chicago O'Hare Intl Airport in November is currently the most expensive (average of $368). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Benton Harbor
Rosemont
Naperville
Lake Geneva
Des Plaines
Glenview
Oak Brook
Aurora
Oakbrook Terrace
Delavan
Schaumburg
Libertyville
Rockford
Hoffman Estates
Gurnee
Orland Park
South Holland
Beloit
Elgin
Racine

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Toronto to O'Hare Intl

Top 4 airlines flying from Toronto to O'Hare Intl

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$137Average$287FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$193Average$319FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$195Average$282FlexibilityNo cancel feeOn-time69%
Porter AirlinesCheapest$207Average$347FlexibilityNo cancel feeOn-time52%

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